HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 5-(Dimethylphosphoryl)-3-methoxypyrazin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 5-Bromo-3-methoxypyrazin-3-ylamine | HCID 67052669 | — |
| Reactant | methylphosphonoylmethane | HCID 178503022 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Product | 5-(Dimethylphosphoryl)-3-methoxypyrazin-2-amine | HCID 67052682 | 63% |
Reaction Steps
To a solution of 5-bromo-3-methoxypyrazin-3-ylamine (0.204 g, 1.00 mmol) in 4 mL DMF was added dimethylphosphine oxide (0.171 g, 1.10 mmol), palladium acetate (11.0 mg, 0.0490 mmol), XANTPHOS (35.0 mg, 0.0600 mmol), and potassium phosphate (0.233 g, 1.10 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150° C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane) to afford the desired product (126 mg, 63% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09273077B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-29c7c4a2c65e4b50943190731e0fd74f |
| Source note | uspto-grants-2016_03 |